Annapolis Vacation Packages
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Your Annapolis Vacation
Pick a Annapolis vacation package and focus on what counts — having some fun. No more planning headaches, just a lot more free time to uncover what's special about this lively city, such as its rich history and coastal scenery. Fill your days with tours of K Bridge Recreation Area, Crane Lake Recreation Area and Walnut Hollow Lake, some of the attractions you should see during your trip to Annapolis. A couple of quick clicks is all it takes to build a customized Annapolis vacation on Expedia.
Top Annapolis Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Wildwood Hotel
CA $1,030
per person
Sep 25 - Sep 28
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Louis (STL)
9.2/10 Wonderful! (1,672 reviews)
Very nice hotel in a very nice neighborhood. It felt safe and comfortable in the community since we were trying to avoid the downtown St Louis area and its traffic.. Our room was with a balcony which the front desk was very helpful in arranging for us. I would go back for sure if traveling in the area.
Reviewed on Aug 9, 2026
The Cheshire
CA $1,172
per person
Sep 25 - Sep 28
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Louis (STL)
8.8/10 Excellent! (1,006 reviews)
When checking in, the staff woman was less than friendly. There seemed to be a situation with another upset guest that may have caused the unpleasant nature. Once we entered the room, we noticed right away a musty smell. The AC did not seem to be working correctly. Though it never got hot, it also never got any cooler. The furniture had visible stains and a few of the pillow cases had staining as well. The pillows themselves are downed pillows and once you lay on them, they flatten out thin. We requested a few extra pillows that were supposed to be brought to our room which never arrived. We requested more towels which were also supposed to be brought to our room which also never arrived. Breakfast on morning one for us which was Sunday was great, however it was apparent that the fruit and pastries were being reused daily and by our check out morning on Tuesday they were no good. The pool area was decent. You have to reserve the canopy so it was unusable to us. Overall, our stay was okay. I wouldn’t say it was awful but I wouldn’t say it was great either. We don’t intend on staying in the future.
Reviewed on Aug 9, 2026
Ready to book your vacation to Annapolis?
Annapolis Hotel Deals
Rustic River Cabin Getaway
Annapolis MO
9.8/10 Exceptional! (85 reviews)
"The cabin was awesome. Had a girls trip with lifelong friends of over 40 years. We enjoyed the disconnecting and relaxation it offers. There is no cell service so it was nice to chill, play games and catch up and reminiscence of our friendship over the years. The river is a small walk down the road. ..."
Reviewed on Jun 28, 2026
Relaxing 3B Log Home-15 min walk to the Black River!
Annapolis MO
8.8/10 Excellent! (12 reviews)
"This luxury cabin was the perfect getaway. For a remote location it has everything to keep a family busy happy and comfortable. The little details so well thought of from all the kitchen amenities to full closet of family games for the little and the older. Plenty of towels and blankets all clean ..."
Reviewed on Jun 23, 2026
Panther Den Cabin is located 4 miles from Hwy K Campground
Annapolis. MO
9.6/10 Exceptional! (14 reviews)
The cutest little cabin AKA "The Panthers Den"
"It was seriously so cute! Nice & clean. Plenty of space & sleeping areas for our family of 6. Although, we didnt spend alot time actually in the cabin it was nice to come back to a nice cool place to relax for a bit and shower, after an entire evening in the rain (Friday) & full day of sun floating ..."
Reviewed on Jul 20, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Annapolis attractions
K Bridge Recreation Area
9.6/10 (4 reviews)
Explore the great outdoors at K Bridge Recreation Area, a lovely green space in Annapolis. While you're in the area, stroll along the riverfront.
Walnut Hollow Lake
Commune with nature and explore the great outdoors at Walnut Hollow Lake during your travels in Annapolis. Wander the parks and riverfront while you're in the area.
Frequently asked questions
How much does an Annapolis vacation package cost?
Offering excellent value package deals from CA $1,030 on Expedia, you'll be pleasantly surprised at how much a vacation to Annapolis costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Annapolis?
Plan your getaway for the off-peak season and you're likely to find cheap Annapolis vacation packages. Remember that public holidays and local events and festivals can have an impact on prices, so do your research before booking.
How many days is enough for Annapolis?
With a well-organized schedule, you can easily visit the top Annapolis sights in a handful of days. But if you prefer to explore off the beaten track or take day trips, consider booking your Annapolis vacation for longer.
How to find the best Annapolis package deals?
Use Expedia's filter tool to find some terrific Annapolis package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or browse for Annapolis package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book an Annapolis vacation as a package?
You can enjoy significant savings on your Annapolis retreat by booking a customized vacation package. Click on the "Package" heading, then select your travel dates and destination to view some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Annapolis?
Score incredible bargains by reserving your flights early with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for a spur-of-the-moment Annapolis break.
How to plan a trip to Annapolis?
- Pick your dates: The things you plan to do in Annapolis and your preferred season will help you decide when to go.
- Calculate your budget: Ensure you have enough money to cover everything from transportation and meals to activities and airfares. Your hotel will likely be the largest expense during your trip to Annapolis.
- Work out your trip length: Think about how long you'd like to spend discovering Annapolis. Plan your days so you can get to all the experiences and attractions you're interested in at a leisurely pace.
- Combine your accommodations and airfare: Once you've nailed down your trip dates and duration, book the perfect Annapolis vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
